Head to your accommodations at Hotel Haya, a modern boutique hotel situated in the heart of the historic Ybor City neighborhood near downtown Tampa. Once you’re settled in, walk a block to begin exploring 7th Avenue, Ybor’s most popular street.

Founded in 1886, Ybor City is full of history and culture and it’s a lovely place for leisurely exploration by foot. To learn more about the city’s history as an immigrant melting pot and cigar-making capital, visit the Ybor City Museum, housed in a bakery from the 1920s. Afterward, stop by Chill Bros. Ice Cream for a scoop of homemade pistachio. 

Grab dinner and drinks at your hotel at Flor Fina to celebrate the start of your vacation. Flor Fina combines Mediterranean and Latin cuisines with local Gulf Coast inspiration, including a rotating menu of ceviche.

Start your day on the Tampa Riverwalk. Begin at the Florida Aquarium and stroll west along the water. You’ll pass grassy pocket parks, breweries, museums, shops, and restaurants. For breakfast, stop into Samaria Cafe for their fluffy omelets, eggs Benedict, and gyros. Then, absorb the Tampa Bay History Center and absorb the local history from pirates to cigars. 

For lunch, head downstairs to the Columbia Cafe, where you can enjoy their famous Cuban sandwich on the patio overlooking the Hillsborough River. Back on the Riverwalk, make a pit stop for a local beer, cocktail, or glass of wine at SIP, the Airstream bar. They’ll even put your drink in an official Riverwalk cup so you can continue on your journey. 

For a distinctive experience in downtown Tampa, check out nearby Meacham Urban Farm, which grows and sells its own organic vegetables, sourdough breads, local meats and eggs, honey, ferments, and fine pantry goods. Shop small and support the local business by grabbing gifts to bring home to family and friends. 

Turn up the romance tonight with Bern’s Steakhouse where you can have a “Champagne and Caviar” among other delights. If you’re not too tired, check out Gin Joint for a nightcap and craft gin experience. Suspender-clad waiters serve their vast selection of gins, with live jazz frequently playing in the evenings.

Ready to add some sand and sea to the equation? Start part two of your trip by checking into Hotel Zamora, an oasis with a Mediterranean feel on St. Pete Beach. Suites include spacious waterfront king rooms with soaking tubs. Choose your own adventure today by renting kayaks, bikes, paddleboards, or fishing poles directly from the hotel and enjoy the area’s outdoors.  

Fifteen minutes from the hotel is John's Pass, a 19th-century fishing village that is now a mecca of shops, eateries, and activities. Rent jet skis, take a dolphin-watching cruise, or play Skee-Ball at the arcade, while keeping an eye on the sky so you can make it back to the beach by sunset. 

To celebrate your first St. Pete Beach golden hour, rent a beach cabana from Cabana Club. Your personal concierge will set up everything: cabanas, umbrellas, lounge chairs, ice-filled coolers, a Bluetooth speaker, and sunscreen.

Today starts in downtown St. Pete with a sun-kissed walk on the new St. Pete Pier. Take your pick along the way for snacks to nibble on, sit-down lunch restaurants, or cold drinks. Enjoy live music, public art exhibits, and other rotating events which set up shop on the pier. When you’re finished, head to the nearby Dalí Museum which houses the largest collection of his works outside of Spain.

Only a 10-minute walk from the start of the pier and you’ll reach Vinoy Park, an ideal place to kick back and relax with a picnic. Take a peek over the seawall and spot the dolphins that frequently populate these waters. Stop to smell the roses on a walk through North Shore Park’s arboretum and its many exotic plants from around the world. Continue your walk along North Shore Drive to enjoy the old Florida architecture and (if you visit in early summer) blooming poincianas. 

Back in downtown St. Pete, take a walk on Central Avenue. Cage Brewing has a laid-back atmosphere and frequent live music performances. Stop at Trophy Fish to enjoy their fresh catches while supporting local fishermen and enjoying the laid-back, nautical vibe of their outdoor dining area. 

As the sun gets ready to set, venture back to St. Pete Beach, this time aiming for the Dewey Rooftop Bar at the Berkley Beach Club Hotel. Enjoy the sunset with a glass of wine and oysters and views overlooking the Intracoastal Waterway and the beach.

End your Florida trip with a night in Sarasota at the Lido Beach Resort, about an hour’s drive south of St. Pete Beach. Start the day with a visit to the Ringling Circus Museum, where you can squeeze into a clown car or climb aboard the train that John Ringling used to travel across the country. You can tour Ca’ d’Zan, the home of the Ringlings, modeled after their favorite Mediterranean Revival architecture, opulently furnished, and well-stocked with china collections and crystal chandeliers. Also on the Ringling grounds is the Asolo Repertory Theatre, which stages new works, reinterpreted classics, and musical theater productions. 

Linger at the beautiful grounds of The Ringling for as long as you like and grab some food for a picnic or dine at the Ringling Grillroom. Experience more of the area’s renowned Modernist architecture on a Mid-Century Architecture Home Tour. Or surround yourself with nature in the afternoon on a visit to the Marie Selby Botanical Gardens. Take some quiet time among the Florida flora to digest the whirlwind experiences of the past five days. For dinner this evening, celebrate the last night of your trip by choosing from Ophelia’s on the Bay for romantic waterfront views or the Melting Pot for a fun fondue experience.